Recently, I begrudgingly gave in to a desktop OS upgrade on my personal laptop. Know what it bought me? Nothing. It didn't solve a problem. It didn't let me work better or faster. It merely "kept me up with the latest tech."

That's essentially what the return on investment will be when hundreds of thousands--perhaps millions--of enterprise desktops get upgraded to Windows 8. Surely we can figure out something better to do with all that money, even if we have to move some cheese in the process.

And that's where my inner finance child starts struggling with my tech self who's committed to keeping things rolling along. I see my staff and users happily and productively ensconced in the Windows world. I want them to be happy and productive, but I want to get rid of unnecessary ongoing expenses, too, even if it causes temporary pain.

How much money are we talking? For a midsize company with 5,000 desktops, between $2.5 million and $3.5 million. To get that number, I set some likely conditions around our investment scenario. As a practical matter, when companies move to a new desktop OS, they almost always invest in new hardware, too. Yes, Microsoft has assured us that Windows 8 will work fine on any PC that can run Windows 7. But organizational memory says that an OS-upgraded PC is a flaky PC. Don't mess with those battle-scarred IT veterans--it's out with the old, in with the new.

Conventional wisdom also holds that if you're going to touch the PC, you might as well give desktop users completely new workstations, probably with new monitors, as an apology for the hassle of learning a new user interface and other sundry inconveniences. Hardware is, after all, "cheap," and giving customers that virtual new-car smell is good IT PR. Assume that you can resell those retired workstations for about 20 or 30 cents on the dollar paid and that there's automation in place for deploying applications and user data.

With assumptions out of the way, let's talk money. Say that for $500 you can get a new system that can handle word processing and accessing your ERP application via various permutations of Web and (shudder) green screen. A 20-inch monitor costs $150 and 17-inch one $100. Consider whether you're going to make your desktop customers unhappy by giving them the smaller versions just to save $50.

Will you buy the $100 PC warranty? Many large shops do, but to be conservative, let's say that you pass. The cost of self-maintenance is probably more than $100 per workstation, but it's the same whether you replace the PC or not, so we'll leave that out. Assume that you're paying $20 per hour for either a deployment contract or labor, which is incredibly conservative if you consider the fully burdened cost (healthcare and other benefits) of an employee. Call it a conservative 30 minutes of time per fully automated deployment once you deal with the help desk calls and oddball scenarios your staff will be on the hook for. We'll consider staff time as a real cost.

Add it all up, and we're talking in the ballpark of $610 per Windows 8 workstation, assuming everything goes right. Your 5,000 desktops have cost the company a cool $2.55 million without monitors, and $3.05 million with them. Pretend that deployment labor doesn't exist, and you're still spending $2.5 million to $3 million. That's quite a nice-size project, budget-wise.

Now let's say that your boss just hired the Limor Fried of CFOs: young, very technology savvy, and a barracuda when it comes to what she does best--which is finance. When you're a finance barracuda, you're serious about keeping expenses low and return on investment high. So the first question she's going to ask is, "Why, exactly, do we need to do this? What's the benefit to the business, and what's the risk if we don't upgrade?"

That's exactly the conversation Microsoft doesn't want you to have.

No business prioritizes projects that don't deliver tangible value. Most will grudgingly OK projects to keep the wheels from falling off the car--but not if there's a contrarian questioning, rightly, whether you'd be smarter ditching the car and taking public transportation.

Your CFO may not be a tech-savvy barracuda, but someone in the C-suite eventually will (or should) ask what business value mass desktop OS change-outs actually deliver, whether the wheels are really about to fall off, and what the alternatives are given that 90% of your computer users don't do anything more taxing than browse the Web, write memos, work on spreadsheets, and use the ERP system. Do you really need a next-generation OS to do that? No. And if you as a CIO try to argue otherwise, you're risking your credibility.

So What's Your Alternative, Smarty-Pants?

I'll admit here and now that jumping off the OS upgrade treadmill is difficult. But you'd better have some suggestions on how to start weaning users from fat, expensive Wintel hardware, because someone will eventually demand an alternative plan.

The biggest bang for your buck will be gained by either installing a freely available Linux desktop operating system on existing hardware or, for some roles, dropping PCs altogether and going mobile.

There are several problems here. Linux will be a bombshell for your support staff, many of whom have no idea how to deal with the OS, although it's likely you're using system management and deployment tools, like Kace's KBOX, that support Linux desktops. End user acceptance also will be a problem, although probably less of one than you think given that today's all-digital and cloud-delivered options make Linux adoption more of a training and policy question.

Remember: End users want multimedia centers--they want to create spreadsheets and listen to music while they do so. Delivering on that is less of a problem nowadays because it's not about supporting hardware, like DVD drives, anymore. Even if Linux kills support for an optical drive on last year's crop of laptops, who cares? Media has largely moved online. Smartphone sync via USB to the workstation used to be a problem. Now we have widespread "over-the-air" sync. And mobile device management tools, like AirWatch and IronPort, that allow for app management, actually deliver value, unlike, say, a desktop OS replacement project. And, while proprietary video codecs with spotty OS support have been problematic in the past, that's not so much the case nowadays. Sites that don't offer HTML5 and Flash probably aren't sites that your organization cares about giving users access to. If you really need legacy Win32 support, thin clients or VDI are a good bet. Yes, desktop virtualization is a bridge technology at best, but if that's what it takes to wean your end users off fat desktops, it's worth considering.

If your company is moving to SaaS, private cloud, and Web-based ERP technologies, you don't need to be on the Microsoft and Apple desktop treadmills. All you need is a system with a reasonably up-to-date browser and the ability to push security updates. The problem is that many so-called "Web" ERP technologies actually require Microsoft-only plug-ins to run. Holy ActiveX '90s, Batman! But it appears that this problem is being solved as the lumbering wagons of ERP software production update their underlying Web technologies to be only 10 years old rather than 20.

Your software providers had better understand that it's not a Windows world anymore. If they plan to provide business value via mobility--and if they don't, the competition will--their apps need to run on Android and iOS. Win32 and Win64 aren't the future.

Before discussing Windows 8, regroup and have the difficult conversations about the value of operating system and PC upgrades. Look at this big expense and possible alternatives in terms of finance and business. You'll get some push-back, so enlist allies in finance and on the executive team. Swearing off Windows is a paradigm-buster to be sure. But get started. Figure out how much it will cost to evaluate your needs and create an action plan.

First java was going to kill Windows, then the browser was going to kill Windows, then iOs was going to kill Windows. Windows is a cockroach, it's not going to be killed. Windows will survive a nuclear holocaust.

At last! A note of sanity among the Billyware hype which has, woefully, lasted for too many years. The gui-pretending-to-be-an-operating-system has well and truly had its day and, amid almost daily horror stories of new exploits, malware, hacks (and, of course, the bugs which are de rigeur for Billyware releases) it's time to let this particular overbloated whale die on the beach.Linux isn't hard to support or use, provided people can learn to adapt to a different colour on the desktop background. Apart from that Ubuntu and Linux Mint look so much like Windows that it's frightening. Seriously, though, I think the 'cyberwarfare' we hear so much about will be a deciding factor in the policy-making process of many companies. If you have real data to protect, you don't really care about the multimedia capabilities of your computer and, on the bright side, installing the humble Linux over Windows on any over-spec'd Intel box will give a performance boost like you wouldn't believe...Me? I run Solaris :)

wow, your contract is horrible. As a consumer, I can't even get close to the price of the business computers - the price cuts for business are that good. Either a) you are bashing Dell or b) you need to really look at your contracts.

It saddens me that all this finance jargon and number crunching ended up as yet another "Linux should replace Windows" article. Once again, just like in the real world, a finance guy crunches numbers without considering the real world parameters and side effects.

The prices given are street prices for consumers. Sadly, business plans of the major vendors like Dell easily double the prices. I got myself a decent desktop system for home for a bit over 600$ with a good chunk going for a W7 license. At work I get a Dell that costs twice as much and has half the performance if that.As always, nobody gets fired for buying Dell or Microsoft. I'm not so sure about that when proposing to ditch MS Office for OpenOffice and replace any OS with Linux where only browser based apps are needed, even if it costs tremendously less. That may change if the OOo folks manage to package OpenOffice with a suitable Outlook / Exchange replacement.

Sadly, Linux is not really an operating system, in that binary shipped software is not compatible across different systems that use the Linux kernel. This means it's not an alternative to Windows even if we wanted it to be. Linux is an embedded system, mostly used to build server-appliances that serve webpages, but also used to create a fractured list of desktop operating systems such as "Ubuntu 11", "Ubuntu 12", "ChromeOS" and "Android"...

These all use Linux, but binaries compiled for them are not compatible with each-other. This unfortunately makes any of them a very fractured and difficult market to support 3rd party applications within.

Further, the dream of abandoning software for the browser is a dream that only works in very very limited situations. Many types of client software are still out of the reach of the limits of web-based Javascript development. The post-windows solution has already arrived in the form of "consumerized operating systems" such as iOS and Android. The distinction being, applications in these systems are sandboxed from each other and controlled in such a way that a naive user clicking on any buttons/linux/etc can't generally break the operating system -- because applications do not have the permission to do anything that would break the operating system. This is a big reason we're more satisfied with mobile operating systems than desktops.

Application sandboxing makes these systems dramtically less vulnerable to viruses, malware, and abusive software. "Regular consumers" can uninstall a piece of software from a mobile device and be assured it's totally gone, something that is not true on legacy desktops like Windows and MacOS. This is where we need to be headed, and the fact that Windows8 focused on desktop/touch UI integration instead of sandboxing is a big mis-step.

Even Mountain Lion made a baby step towards "consumerization"; by introducing a preference defaulting application installs to restricted signed apps. This isn't going far enough, but it's going futher than windows8. The next truly successful x86 desktop operating system will embrace consumerization and sandboxing. Will it be Android-x86? iOS-for-desktops? or WIndowws-14? Who knows, but it will happen.

Linux is still a viable option. Just because the tech staff doesn't have the support skillset for it right now, how long would it take to gain it? What is the 3-year or 5-year TCO vs. needed features and qualities (equation for value)? For a reasonably large company, it's not that difficult to run a pilot one year and begin rolling out the next. One to two years is plenty to learn to support a new OS. And if you pay for extra training, your TCO improvement over time will probably still look appealing. Windows will still have to be around for some folks, because of certain apps, so identifying the users and their needs is the critical first step. Some of them can either use a tablet or inexpensive Linux desktop or laptop and rely on web apps, possibly including Google Apps or Office 365, for the normal documents, spreadsheets, and presentations.

BTW, one trend I've seen is employees buying Macs then ALSO buying Windows and running it in a VM on the Mac (they do this for "corporately supported" Windows apps or specific apps that are only available for Windows). So not only does the company pay extra for the Mac premium, but they pay again for Windows!

And then we can start talking about BYOD, right? Who cares what PC the employee brings to work! It's kind of like day laborers or home construction workers or handymen who have to bring their own tools to the job. You want this job? You better bring your computer!